# US 4,395,391 A · Unsymmetrically substituted dicarboxylic-acid-bis-(2,4,6-triiodo-anilides), their preparation, and x-ray contrast media containing same

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- Number: US 4,395,391 A
- Document ID: US4395391A
- Status: Granted
- Kind: A
- Application number: 06/324,368
- Filed: 1981-11-24
- Granted: 1983-07-26
- Earliest claimed: 1980-11-25
- Assignees: Schering Corporation
- Inventors: Heinrich Pfeiffer; Wolfgang Mutzel; Ulrich Speck
- Web page: https://patentgrep.com/patent/US4395391A

## CPC

- C07C 233/00: Carboxylic acid amides
- A61K 49/04: X-ray contrast preparations
- C07C 233/30: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Unsymmetrically substituted dicarboxylic-acid-bis-(2,4,6-triiodo-anilides) of formula I ##STR1## wherein X is straight-chain or branched alkylene interrupted by one or more oxygen atoms, R.sup.1 is --NHacyl, --CH.sub.2 NHacyl, or --CONHR.sup.3 wherein R.sup.3 is hydrogen or a lower straight-chain or branched optionally mono- or poly-hydroxylated, alkyl residue, and where any hydroxyl groups present may be functionally modified, and R.sup.2 is hydrogen or lower alkyl, and their salts, are extraordinarily well suited, in view of their good pharmacological and physico-chemical properties, as water-soluble x-ray contrast media for all fields of application, in particular for i.v. cholegraphy and for computer tomography.

## Claims

### Claim 1

A compound of the formula ##STR11## wherein X is C.sub.1-12 -alkylene optionally interrupted by 1-4 oxygen atoms;
R.sup.1 is --NH--C.sub.2-4 -alkanoyl, --CH.sub.2 NH--C.sub.2-4 -alkanoyl, in both of which alkanoyl can optionally be substituted by 1 or 2 hydroxy or C.sub.1-4 alkoxy groups, or --CONHR.sup.3, wherein R.sup.3 is hydrogen, C.sub.1-4 alkyl or C.sub.1-5 alkyl substituted by 1-4 hydroxy or C.sub.1-4 -alkoxy groups;
R.sup.2 is hydrogen or C.sub.1-4 alkyl;
or a physiologically compatible salt thereof with an inorganic or organic base.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R' is --CONHR.sup.3.

### Claim 3 (depends on 1)

A compound of claim 1 wherein R' is --NH-alkanoyl.

### Claim 4 (depends on 1)

A compound of claim 1 wherein R' is --CH.sub.2 --NH-alkanoyl.

### Claim 5 (depends on 1)

A compound of claim 1 wherein the alkanoyl group in R' is acetyl, propionyl, hydroxyacetyl or .alpha.-hydroxypropionyl.

### Claim 6 (depends on 1)

A compound of claim 1 wherein R.sup.3 is H, methyl, ethyl, hydroxyethyl or 1,3-dihydroxy-propyl-(2).

### Claim 7 (depends on 1)

Hexane-diacid-1-(3-carboxy -2,4,6-triiodo-anilide)-6-(3-carboxy-5-N-methyl-carbamoyl-2,4,6-triiodo-ani lide), a compound of claim 1.

### Claim 8 (depends on 1)

3-oxapentane-diacid-1-(3-c arboxy-2,4,6-triiodo-N-methylanilide)-5-(3-carboxy-5-N-methylcarbamoyl-2,4, 6-triiodo-anilide), a compound of claim 1.

### Claim 9 (depends on 1)

3,6,9-trioxaundecane-diacid-1-(3-carbox y-2,4,6-triiodo-anilide)-11-(5-acetamido-3-carboxy-2,4,6-triiodo-anilide), a compound of claim 1.

### Claim 10 (depends on 1)

An x-ray contrast medium comprising an amount of a compound of claim 1 effective as an x-ray contrast agent and a pharmaceutically acceptable carrier.

### Claim 11 (depends on 10)

An x-ray contrast medium of claim 10 where the concentration of x-ray contrast agent is 50-400 mg I/ml.

### Claim 12 (depends on 1)

A method of visualizing a part of the body comprising administering an effective amount of a compound of claim 1 and then subjecting the part of the body to x-ray diagnosis.

### Claim 13 (depends on 12)

A method of claim 12 which is cholegraphy, liver visualization or computer tomography.

### Claim 14 (depends on 12)

A method of claim 12 which is computer tomography of the liver.